


Pretty Woman

by thesocraticstare



Category: Silicon Valley (TV)
Genre: Anal Sex, Crossdressing, Dirty Talk, M/M, Plot What Plot/Porn Without Plot, Richard is a stupid boy but he means well, Roleplay, and Jared has a fun time
Language: English
Status: Completed
Published: 2017-10-01
Updated: 2017-10-01
Packaged: 2019-01-07 21:23:53
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,828
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12240873
Author URL: https://archiveofourown.org/users/thesocraticstare/pseuds/thesocraticstare
Summary: In case I forget to tell you later, I had a really good time tonight.





	Pretty Woman

**Author's Note:**

  * For [reserve](https://archiveofourown.org/users/reserve/gifts).



Richard comes into the bedroom and sees Jared kneeling in the middle of his bed. The first thing that gets him is the fucking wig. Jared isn't wearing any makeup and he looks—starkly exposed, that black pageboy like a cheap Halloween version of Uma Thurman in _Pulp Fiction_ —the ends brush his naked shoulders and Richard feels himself shudder, imagines what that synthetic hair must feel like—tickling against him, imagines it tickling against his thighs if Jared were to blow him now, wearing this costume, dressed up like this, just for him—

Jared's eyes lift slowly from the bedspread and Richard realizes he's been standing in the doorway with his jaw dropped for like. Awkwardly long. 

He opens his mouth, closes it again. “Uhhh. Wow. Um. You look. Fucking perfect.” He can’t stop staring—at the way the light from the bedside lamp reflects off the unnaturally shiny hair of the wig, at Jared’s broad, sharp-contoured shoulders, the skin so pale it’s nearly translucent, the blue veins beneath almost as startling as his incredible, unbearable eyes. Richard swallows, audibly, half backs out of the doorway, waffles for a moment and then steps back in, closing the door behind him and leaning back against it for support.

His eyes skitter over the vision on the bed. Jared has brought up roleplay a couple of times, always with his habitual mix of cheerful enthusiasm and gentle recognition of Richard’s anxieties, which haven’t been alleviated since they started fucking regularly, only shifted to focus on things Richard finds, if anything, even more impossible to talk about. But Jared is unfathomably patient. He’s smiling, now, his eyes relaxed, spot-lit by the soft glow of the bedside lamp. Richard swallows hard again and takes one tiny step forward. 

“Hey. Um—wow. Jared. You’re really—I mean. Actually. Should I, um—call you something… else?” Richard takes another, tinier step forward. He feels deeply unsteady, like the room’s gravity has shifted completely and he might at any moment fly straight upward, bounce off the ceiling. Jared’s smile deepens; he stretches out one leg—impossibly long—from beneath himself, points it for a moment at Richard, then resettles, making himself more comfortable. 

“You can call me whatever you want,” Jared says. His voice is pitched maybe a little softer than usual, but it’s still utterly recognizable—he’s still so unerringly himself, even dressed so seductively, so wantonly. Richard feels like his blood might be on fire. Jared’s wearing some kind of red corset top—Richard’s never been great at identifying girls’ fashion choices—and when he shifts, Richard’s eyes are drawn down to how it accentuates his slender, attenuated torso. He looks gift-wrapped. Richard takes another step towards the bed and Jared smiles up at him, leans back a little, invitingly. A couple inches of his stomach—which is both concave and perplexingly soft, Richard has learned, to his profound delight—are revealed between the bottom of the corset top and the waistband of some kind of almost see-through, ridiculously short skirt. 

Every detail of this outfit feels intricately designed to turn Richard on. Early in their—relationship (it feels almost like asking for trouble when Richard calls it that, even within the confines of his own mind; he’s always only ever fucked up relationships) Jared had casually mentioned some of the odder fetishes of his past lovers (and how much worse to label himself with that word—he pales a little to even think it), and since then Richard has searched himself for anything similar, worried he’ll run up against something that will force Jared from him. Or, more worrisome to think, Jared would never run, would accommodate himself to almost anything Richard wants from him. Sometimes this knowledge makes Richard’s heart race, half with fear at something yet unknown in himself, half with a kind of dark pleasure, the kind that makes him come shatteringly hard when he’s got Jared’s knees bent back up by his ears. Right now those legs are wrapped in black thigh-high stockings, a pair of strappy red sandals on his long, shapely feet. Richard feels like the worst kind of pervert to even be looking at Jared’s feet. But everywhere he looks, every part of Jared’s body, feels purposefully engineered to arouse him. His mouth is almost painfully dry. 

_Gulp._ Jared is still smiling up at him, so sweetly. He pats the bed next to him and Richard takes a breath, finally walks the rest of the way over and sits down. 

“Hi,” Jared says, still so softly. His eyes are so kind. Richard suddenly pictures himself grasping the back of his wig while he forces his dick in and out of his wet mouth. He drops his eyes to Jared’s leg—his long thigh partially revealed through the transparent fabric of his tiny skirt—then drags his eyes up, up Jared’s body, up to his face again. He’s a little flushed. 

“Hey,” Richard whispers. Jared leans a little bit closer. 

“Richard, is this all right with you? I don’t want to make you uncomfortable. But when we talked about it last time, and tonight just seemed so opportune, I thought—”

“Yeah—no! I mean, yes,” Richard says. “This is, um. I mean, a little unexpected. But I’m—I’m, uh. I’m into it.” He can tell he’s blushing hard. He reaches down and takes the hem of Jared’s little skirt—his brain skips a beat, just thinking that phrase, _Jared’s skirt,_ Jared in a skirt, for him—between his fingers, rubs the fabric slightly.

“Did you order this online?” Jared opens his mouth to answer and he adds, hastily, “Wait—don’t tell me, it’s fine. I mean. You look. Really fucking hot.” Jared’s grinning at him a little. Richard takes a deep breath.

“What did you think, coming out here like this, dressed up like this? Huh? Were you trying to—get me hard?” Richard is blushing all the way down his neck, he can feel it, but he also feels suddenly powerful with how Jared’s eyelashes flutter, with how he arches his long back and whispers, “Yes.”

Richard reaches up, a little nervously, and puts his hand high on Jared’s leg. They both inhale. Jared’s wearing a black jockstrap under the skirt and Richard’s eyes get stuck on it for a moment, his hand flat against the naked top of Jared’s thigh, under the skirt and above the band of his stocking. He leans in a little bit more, tilts his head up—their lips brush very softly, just once.

“Did you get dressed up like this just for me,” Richard whispers. It’s not really a question. But Jared nods, his lips parting, and he leans in, and they’re kissing, and Richard wants to touch him everywhere, immediately, all at once.

He’s got both hands on Jared’s thighs, high up under the skirt, rubbing up and down. Jared shifts a little further up the bed, spreading his legs a little more, giving him better access. He’s very obviously hard, dick pushing up against the skirt a little obscenely. Richard’s mouth waters—he wants to suck it, can’t stop touching Jared’s legs to do it, running his palms over the strange satin-smoothness of his stockings again and again. 

“Oh fuck,” he says directly into Jared’s sweet mouth. “God. Can I put my hand in your panties? Please? Fuck.” Jared takes his hand and pushes it down inside the waistband of his skirt, his underwear, and Richard wraps his hand as fully as he can around Jared’s dick, feels it pulse, so hard and hot. He groans, wrenches his mouth away from Jared’s.

Richard leans away enough to watch his hand in action, squeezing Jared’s dick, watching how his face contorts in pleasure. 

“Fuck! You’re so—fucking nasty—you nasty girl—you like it—don’t you? Getting jerked like this—” Richard crushes his mouth down on Jared’s before he can make any response. When he pulls back his eyes flick between Jared’s face—eyes closed, mouth open and panting—and his own hand flying over Jared’s dick. 

He pushes his hand a little further down, a little uncomfortably constricted by the jock Jared’s wearing, and curves his fingers around Jared’s balls, squeezing them a little, pressing back as far as he can. Jared gasps. 

“Oh fuck—shit, you feel so good. Is this okay? I just—god, I love how you feel.” Richard feels like his brain is fizzing a little but he registers Jared nodding frantically above him, and that’s all he needs. “Oh, good—good girl. Fuck. So good.” His other hand is rubbing over the band of one of Jared’s thigh-highs, fingers brushing over the smoothness of the nylon stocking, the raised lace pattern on the cuff, then Jared’s soft, soft skin in turn. 

Jared leans back a little further, making it easier for Richard to get his hand down inside his jock, cup it around Jared’s balls. Richard’s breath stutters for a moment and he closes his eyes; when he opens them again he sees Jared’s trained on his face, a bit of that gentle smile from earlier still flitting across his features. Richard leans himself up, stretches a little awkwardly over his own arm, his hand still down in Jared’s underwear, still wrapped around his balls. Jared’s dick nudges wetly against his wrist. Richard noses below Jared’s ear—finally feels the strands of synthetic hair touching his own face, just as softly scratchy as he had imagined.

He whispers, breath hot against the corner of Jared’s mouth, “You’re so fucking beautiful. God, I love your dick. Do you want me to fuck you? Can I put it in you? Please, Jared.” Jared’s nodding, humming his assent. Richard’s one hand slides slowly down Jared’s thigh, onto the bed at his side; he draws the other out of Jared’s underwear, gently gripping his sharp hip for a moment, before Jared squirms further up the bed, turns fully onto his back. 

He’s flushed, breathless, still smiling up at Richard, come-hither and somehow a little innocent, this combination something Richard has noted before when they’ve fucked, something that drives him crazy, makes him want to bury himself in Jared until they both lose it, until Jared’s crying out for him in helpless pleasure—something that’s been startlingly common when they’re together, something Richard has never experienced, even thought to experience with another person. Richard pulls off his hoodie, gets tangled for a moment in his t-shirt, unzips his jeans and toes his shoes off, all this while wriggling up the bed and into Jared’s arms.

They kiss again, Jared’s mouth pulling his in magnetically—he tugs it away to kiss Jared’s chin, reveling in how sharp it is, a little prickly with stubble, then fastens their lips together again, moaning against Jared’s mouth. His hands curve around Jared’s shoulders, these also sharp, firm where he presses in his fingers, then down his upper arms, stroking the soft skin of the inside of his arm reverently, drinking in Jared’s little reactions, feeling his smile by touch.

Jared catches one of his hands and his smile curves into something a little mischievous. “Can I show you something?” he whispers. Richard nods, wide-eyed. Jared draws back, turns onto his front, and pulls his knees up under himself, turning to look back over his shoulder. Richard gasps. 

“Do you want to fuck me, Richard?” he murmurs. “I’m ready for you. I want you. Come take what’s yours.” His knees slide a little further apart on the bed, his legs spreading, showing a little bit more of his ass, the end of a plug glinting unmistakably. Richard’s on him in a flash.

“Oh fuck! Jared—are you really—are you fucking serious—” His hands scramble up Jared’s legs, push his skirt up so he can get a better look. Jared arches his spine back down, spreads his knees even wider, angling his hips up, as Richard strokes his hands hard over his ass, staring down at the plug. Richard’s never seen one in use before—is almost scared to touch it, but he reaches out one trembling finger, jostles the base a little. Jared moans.

“God—I’m gonna—oh fuck—” Richard takes a breath, takes both of Jared’s hips in his hands. “You fucking dirty girl. You couldn’t even fucking wait for me, could you? You had to have something inside—” Jared moans again, nodding. Richard snaps one of the bands on his jock, watches Jared’s pale ass quiver. “Oh, God. I’m gonna pull it out, okay? I’m gonna put my dick in you. Is that—do you want—”

Richard pushes his jeans off, his boxers, straddles Jared’s hips from behind. Jared looks back at him again, panting a little, his face so open, wanting him. “Do you want this?” Richard asks, trying to mask his voice breaking a little. 

“I want it. Go on. Oh, Richard, I want you,” Jared says, arching his back a little more. He makes a soft sound when Richard touches the base of the plug again, then a louder sound when Richard grasps it more firmly. Richard pulls it out a little way, then pushes it back in; once, twice, then a third time. His eyes are riveted on Jared’s hole, pink and glistening very slightly. Before they started fucking he had been ashamed at how hard he got off to gay porn—how often he watched it, usually as late at night as possible, when he was fairly sure everyone else was either asleep or fully concerned with their own masturbatory problems. Now he stares in open amazement at Jared’s tiny ass, full of the unyielding plug, listening to him moan as Richard pulls and pushes it again and again.

“Oh—Richard—please—” Jared gasps, and Richard startles as though coming out of a reverie. “Do it—please—you can fuck me—”

“Oh—shit! Okay,” he pants back, stroking Jared’s ass again, half lying on top of him. “Okay. I’m gonna—hold on.”

Jared twists around a little, rolling onto one hip; the other is cocked up by Richard’s waist, and he notices for the first time a condom stuck into the top of one of his stockings. “Shit,” Richard breathes again, awed. He snatches the condom out, tosses it onto Jared’s lower back when he turns over again onto his front. “You really planned all of this,” Richard whispers, running his hands over Jared’s ass again, feeling it up greedily, squeezing it a little, pressing his cheeks together and then pulling them apart, teasing himself, watching the base of the plug glinting each time he holds them open. 

Jared looks over his shoulder again. His wig is a little askew, Richard notices. He’s so hard he doesn’t know if he’ll be able to last more than a minute once he’s actually inside. “It’s all for you,” Jared says simply. His eyes are so blue.

Richard takes hold of the base of the plug and pulls it slowly, steadily out, his mouth open—he shoves it back in, once, hard, when it’s almost all the way out—Jared shouts—then he pulls it back again, this time completely, dropping it onto the bed. He’s straddling Jared’s hips, holding his ass open with both hands, hearing his own breath, his own heartbeat, echoing in his ears. 

“Jared,” he whispers. He swallows, feels overcome by a deep tenderness. “I'm gonna treat you so nice, you're never gonna let me go.” Sometimes, when Richard says or does just exactly the right thing, Jared lets out a sort of cry that’s half a sob, half a laugh, that always catches Richard off guard, even when it’s in response to his corniest lines. Their eyes meet over Jared’s shoulder: his face is pink, he’s smiling so hard he looks like he’s about to cry. Richard snatches the condom back up, reaches over to fumble for the lube in the drawer of the bedside table.

Getting to be inside Jared is—incredible, a pleasure so intense Richard isn’t convinced it shouldn’t be illegal. He lubes up his dick, reaches down, spreading Jared’s ass again—Richard mutters “Fuck” under his breath, lining himself up, his own hips twitching forward, feeling so excited, so painfully ready to be in him. 

“Fu—uck—oh—” He’s tried to keep himself quiet during sex before, usually unsuccessfully. He knows Jared likes it when he’s loud but he feels his face flushing, inasmuch it can with most of his blood supply currently pounding in his dick, the head pressed just inside Jared’s asshole. Terrible things start bubbling up in his chest—he grits his eyes tightly closed, then opens them to watch himself push slowly, so slowly further inside. They’ve talked about roleplay but not—he doesn’t want this to turn weird—weirder than it already is, so hot and so good he already feels himself close to coming, can feel that he won’t be able to shut himself up—

“Fuck, Jared, you’re such a. Such a. Fuck! You’re such a perfect slut,” Richard gasps, the last word almost soundless, almost just breath. He’s gripping one of Jared’s ankles in one hand, his hip with the other, watching himself press further inside Jared’s slick hole, so slow, making them both want it so much, holding himself back as much as he’s able. He sees Jared’s fist clench on the bed, hears him moan.

“Yes! Oh! Richard—I am—I’m just your slut. Just for you. Nobody else,” Jared says. Richard sobs, squeezes his hand tighter around Jared’s delicate ankle. 

“Oh thank you—oh thank you—” he says, inanely, starting to thrust in earnest. Feeling Jared stretch around him, so tight and so hot, so ready for him, accepting him— “Jared! Oh, I love—You fucking bitch. You’re so good—you’re—I love fucking you like this. God, I’m gonna fuck you so goddamn hard. You fucking slut. You wanted this so bad—oh god—” Richard grabs Jared’s skirt and hauls his hips further up, letting go of Jared’s ankle and pushing his head down into the mattress, spreading his fingers through the dark synthetic strands of the wig, feeling Jared’s cries vibrate up through his hand, his arm, into his body, penetrating his heart.

Richard has watched a lot of porn in his day and still feels embarrassed by nudity, his own and others’, but something about Jared—his unselfconsciousness, his frankness, his good-natured acceptance of his own gawky body—makes Richard feel liberated when they’re together like this. His own body feels like it makes sense when it’s inside Jared’s body, like Jared is fixing him, remaking him somehow—like Jared transmutes his hangups into sexual power, somehow recasts him from his base, trembling self into some kind of—well, not quite a sex god. But Jared’s moaning, crying out, saying his name, and Richard is holding tight to his hips, riding him as hard as he can, feeling his mouth drop open as he pounds Jared’s ass. He’s never felt particularly boastful about his own prowess but Jared makes him feel—like he can make it good for him, can please him, bring them together into this hot, intimate world of just the two of them, sharing one body, one breath.

“I’m gonna come,” he hears himself say, his own voice just a hoarse gasp, feeling like something entirely outside his control. His hips are snapping against Jared’s, his dick throbbing. He reaches down and cups Jared’s balls again—hears Jared cry out for it—fondles them in his palm, bent over Jared’s body, his hips a blur. He feels the smoothness of Jared’s stockings rubbing against the insides of his own thighs, the friction almost burning—he lets out an animal sound, a kind of anguished yowl—he grips Jared’s tight little ass in both hands, bruisingly hard, and comes, his vision blurring.

It takes him a minute to regain a little equilibrium, but then Richard reaches down, slips his hand under Jared’s hard, shuddering flank, and palms his dick, wet through the fabric of his jock. Jared cries out again when Richard pushes his hand back inside, roughly jerking him again, pitching forward until his mouth is right next to Jared’s ear and he’s panting directly into it, the glossy hairs of the wig buffeted by his laboring breath.

“Perfect—gorgeous—come for me,” Richard whispers, eyes closed, coming back to himself enough to feel a little embarrassed by what he’s saying, even though he knows Jared likes it, even though he can feel Jared’s dick getting wetter in his hand, so close. He reaches back and grabs Jared’s leg again, slipping down the length of his calf, over his ankle, feeling how his toes are curling, feeling his breath growing shorter and shorter—

“Richard! Oh—darling—yes—just—for you,” Jared gasps, and then he’s shuddering, coming hot and wet in Richard’s hand. Richard tips over slowly, coming down on his side and pulling Jared back with him. He leaves his wet hand in Jared’s underwear for the time being.

They take a moment just to lie together, breathing slowly returning to normal. Richard still feels like his head is buzzing, his body still glowing a little with—whatever alchemy it is that Jared does to him, turning his desires into reality. He gingerly removes his sticky hand and tries to wipe it surreptitiously on the bedspread before wrapping both arms around Jared from behind, pressing his face into Jared’s sweaty neck under the wig. Richard licks and then nips, very gently. Jared giggles, then turns around, tucking himself against Richard’s body. Richard knows Jared likes this part almost better than fucking itself, strokes his back gently, running his hand almost absent-mindedly over the ties of the corset top.

“Richard,” Jared says softly. Richard hums. “That was perfect. You were magnificent.” 

Richard slightly adjusts Jared so that he’s lying with his head pillowed on Richard’s collarbone—not exactly comfortable, probably, but easier to see his face. His hand pauses on Jared’s back. “I hope…” he starts. “I hope I wasn’t… too weird. I mean… I don’t think… you know. That you’re.” He blushes. “That there's anything wrong with. Uh, sex positivity? Or like. Being a little s-slutty or whatever. You know. Like, for real. I just…” He chances a look down at Jared’s face.

He’s smiling up at him, that same beckoning, welcoming smile from the beginning of the night, the beginning of this encounter that’s left Richard feeling—drained, yes, but also. Like this love he and Jared have is even realer than he thought. That he can have these things, and make them good for his—his lover, and lie there afterwards, wrapped in a haze of satisfaction, of belonging and being needed. Jared sighs happily, curls himself a little further into the curve of Richard’s body.

“Oh, Richard,” he says softly. “Don’t you know? I’m a sure thing.”

**Author's Note:**

> Inspired by some beautiful fan art by wasongo. This is my first real piece of slash fic—hope it passes muster/sorry it's nothing but unspeakable filth from beginning to end! Many thanks are due to the lovely and wonderful reserve. Extra thanks to the memorable quotes section of Pretty Woman's IMDB page.


End file.
